Apr 3, 2025; Toronto, Ontario, CAN; Portland Trail Blazers guard Shaedon Sharpe (17) comes down with a rebound against the Toronto Raptors during the first half at Scotiabank Arena. Mandatory Credit: John E. Sokolowski-Imagn Images John E. Sokolowski-Imagn Images

2 Key Blazers Facing Prove-It Seasons, Says Insider

Originally posted on Portland Trail Blazers on SI
By Jason Fray | Last updated Sep 17, 2025 2:30 PM ET

The Portland Trail Blazers are in somewhat of a unique situation moving forward.

On one hand, the team boasts two future Hall of Famers (Jrue Holiday, Damian Lillard) in the latter stages of their respective careers. Lillard figures to be out all of this year as he rehabilitates from a torn Achilles. Considering how young the rest of the roster is, getting this veteran duo should be immensely beneficial on and off the court.

On the other hand, the presence of Holiday (and eventually Lillard) could stunt — or even block the progression of the two young guards on the roster with tons of promise in Scoot Henderson and Shaedon Sharpe. Henderson figured to be the odds-on starter at the point guard spot this year given that Anfernee Simons is now in Boston.

However, with the eventual return of Lillard, will Henderson retain his spot a year from now? Sharpe is in even more of a tough situation. It's unlikely Holiday will come off the bench given the team's need for a stabilizing force on the floor with a bunch of young players.

At the same time, if Sharpe is jettisoned to be the team's sixth man, will Portland have enough data in knowing whether it's prudent to eventually pony up the cash for a longterm contract extension?

Shaedon Sharpe – Career Dunk Reel

Not many have hops like this https://t.co/QUyPOTLnP9 pic.twitter.com/t3OUwy91Lw
— RCsWorld (@RCsWrld) September 16, 2025

John Schuhmann of NBA.com recent put together a power rankings of the Western Conference. Portland happened to end up No. 11 in the rankings. One point specifically was brought up about the backcourt rotation — and one big question is posed.

"Scoot Henderson and Shaedon Sharpe need to play a lot, because the Blazers need to figure out what they have in the young duo (21 and 22 years old, respectively) before Lillard comes back from his Achilles tear. Both saw jumps in efficiency last season and both still have plenty of room for improvement. Holiday is versatile enough to play alongside either one, giving the Blazers a pretty unique three-man guard rotation."

Scoot Henderson looking READY for this season pic.twitter.com/FYAxfOqnFQ
— RIPCITYY (@shaesharpeshow) August 16, 2025

Of the two, Henderson seems like a more surer bet to start. We saw evidence of a player that grew last year in a reserve role. For Sharpe, scoring is not an issue. His inability to defend at even a passable level must improve greatly if he's considered anything more than a microwave scorer off the bench moving forward.

Suffice it to say, but it'll be very interesting to see how head coach Chauncey Billups trots out this rotation in the pre-Lillard era.